ME02089B - Inhibiteurs de bêta-lactamase - Google Patents

Inhibiteurs de bêta-lactamase

Info

Publication number: ME02089B
Authority: ME; Montenegro
Prior art keywords: alkyl; compound; sulfoxy; diazabicyclo; octane
Prior art date: 2008-01-18

Application number

MEP-2013-511A

Other languages

English (en)

Unknown language (me)

Inventor

Christopher J Mortko

Ian Mangion

Nelo Rivera

Rebecca T Ruck

Michael Shevlin

Timothy A Blizzard

Helen Chen

Candido Gude

Jeffrey D Hermes

Jason E Imbriglio

Seongkon Kim

Jane Y Wu

Sookhee Ha

Original Assignee

Merck Sharp & Dohme

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-01-18

Filing date

2009-01-15

Publication date

2014-04-30

2009-01-15 Application filed by Merck Sharp & Dohme filed Critical Merck Sharp & Dohme

2014-04-30 Publication of ME02089B publication Critical patent/ME02089B/fr

Links

239000003781 beta lactamase inhibitor Substances 0.000 title 1
229940126813 beta-lactamase inhibitor Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims 57
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 22
OVKXDANNQWXYKF-UHFFFAOYSA-N 2-methyloctanamide Chemical compound CCCCCCC(C)C(N)=O OVKXDANNQWXYKF-UHFFFAOYSA-N 0.000 claims 20
150000003839 salts Chemical class 0.000 claims 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
125000000217 alkyl group Chemical group 0.000 claims 10
229910052799 carbon Inorganic materials 0.000 claims 9
238000000034 method Methods 0.000 claims 9
229910052801 chlorine Inorganic materials 0.000 claims 8
239000000460 chlorine Substances 0.000 claims 8
229910052739 hydrogen Inorganic materials 0.000 claims 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
229910052794 bromium Inorganic materials 0.000 claims 7
229910052731 fluorine Inorganic materials 0.000 claims 7
125000000623 heterocyclic group Chemical group 0.000 claims 7
125000003386 piperidinyl group Chemical group 0.000 claims 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
125000001424 substituent group Chemical group 0.000 claims 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
229910052736 halogen Inorganic materials 0.000 claims 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
239000003054 catalyst Substances 0.000 claims 4
150000002367 halogens Chemical class 0.000 claims 4
NAHBVNMACPIHAH-HLICZWCASA-N p-ii Chemical compound C([C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H]2CSSC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC2=O)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)=O)C(C)C)C1=CC=CC=C1 NAHBVNMACPIHAH-HLICZWCASA-N 0.000 claims 4
-1 0-C1-6 Chemical group 0.000 claims 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
SMOBCLHAZXOKDQ-ZJUUUORDSA-N [(2s,5r)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound O=C([C@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NC1CCNCC1 SMOBCLHAZXOKDQ-ZJUUUORDSA-N 0.000 claims 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 3
125000005842 heteroatom Chemical group 0.000 claims 3
125000002950 monocyclic group Chemical group 0.000 claims 3
125000002757 morpholinyl group Chemical group 0.000 claims 3
229910052760 oxygen Inorganic materials 0.000 claims 3
125000004193 piperazinyl group Chemical group 0.000 claims 3
125000004076 pyridyl group Chemical group 0.000 claims 3
229910052717 sulfur Inorganic materials 0.000 claims 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims 2
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
208000035143 Bacterial infection Diseases 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
229910003204 NH2 Inorganic materials 0.000 claims 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
150000003973 alkyl amines Chemical class 0.000 claims 2
125000006242 amine protecting group Chemical group 0.000 claims 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
125000003725 azepanyl group Chemical group 0.000 claims 2
125000002393 azetidinyl group Chemical group 0.000 claims 2
208000022362 bacterial infectious disease Diseases 0.000 claims 2
150000003939 benzylamines Chemical class 0.000 claims 2
239000003782 beta lactam antibiotic agent Substances 0.000 claims 2
150000004657 carbamic acid derivatives Chemical class 0.000 claims 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
239000003638 chemical reducing agent Substances 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 2
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
229920006395 saturated elastomer Polymers 0.000 claims 2
150000003461 sulfonyl halides Chemical class 0.000 claims 2
MZNBNPWFHGWAGH-UHFFFAOYSA-N tert-butyl n-phenylmethoxycarbamate Chemical compound CC(C)(C)OC(=O)NOCC1=CC=CC=C1 MZNBNPWFHGWAGH-UHFFFAOYSA-N 0.000 claims 2
150000003512 tertiary amines Chemical class 0.000 claims 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
238000002560 therapeutic procedure Methods 0.000 claims 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 2
239000002132 β-lactam antibiotic Substances 0.000 claims 2
229940124586 β-lactam antibiotics Drugs 0.000 claims 2
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 claims 1
NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims 1
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 1
229910004727 OSO3H Inorganic materials 0.000 claims 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
229910006074 SO2NH2 Inorganic materials 0.000 claims 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
AEVFDHXLJVXHNF-ZJUUUORDSA-N [(2s,5r)-2-(4-aminopiperidine-1-carbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound O=C([C@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])N1CCC(N)CC1 AEVFDHXLJVXHNF-ZJUUUORDSA-N 0.000 claims 1
ZYTMUDLKBAIEAQ-SFYZADRCSA-N [(2s,5r)-2-(azetidin-3-ylcarbamoyl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound O=C([C@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NC1CNC1 ZYTMUDLKBAIEAQ-SFYZADRCSA-N 0.000 claims 1
CHULEIUYGBCUPR-MNOVXSKESA-N [(2s,5r)-2-[(1-methylpiperidin-4-yl)carbamoyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound O=C([C@H]1N2C[C@@](CC1)(N(C2=O)OS(O)(=O)=O)[H])NC1CCN(C)CC1 CHULEIUYGBCUPR-MNOVXSKESA-N 0.000 claims 1
XQEJZAYKSCNDRE-ZOCYIJKUSA-N [(2s,5r)-2-[3-(dimethylamino)pyrrolidine-1-carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound C1C(N(C)C)CCN1C(=O)[C@H]1N(C(=O)N2OS(O)(=O)=O)C[C@H]2CC1 XQEJZAYKSCNDRE-ZOCYIJKUSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
239000011260 aqueous acid Substances 0.000 claims 1
239000007864 aqueous solution Substances 0.000 claims 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
229940092714 benzenesulfonic acid Drugs 0.000 claims 1
150000001768 cations Chemical class 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
HMPHJJBZKIZRHG-UHFFFAOYSA-N chloromethanesulfonic acid Chemical compound OS(=O)(=O)CCl HMPHJJBZKIZRHG-UHFFFAOYSA-N 0.000 claims 1
UFJSITOHZAUZBO-UHFFFAOYSA-K cycloocta-1,3-diene;trichloroiridium Chemical class Cl[Ir](Cl)Cl.C1CCC=CC=CC1 UFJSITOHZAUZBO-UHFFFAOYSA-K 0.000 claims 1
DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 claims 1
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims 1
ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
125000003709 fluoroalkyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000007327 hydrogenolysis reaction Methods 0.000 claims 1
229910052741 iridium Inorganic materials 0.000 claims 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
125000003965 isoxazolidinyl group Chemical group 0.000 claims 1
229940098779 methanesulfonic acid Drugs 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
150000004682 monohydrates Chemical class 0.000 claims 1
VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims 1
125000005961 oxazepanyl group Chemical group 0.000 claims 1
125000000160 oxazolidinyl group Chemical group 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 claims 1
125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
229910052703 rhodium Inorganic materials 0.000 claims 1
239000010948 rhodium Substances 0.000 claims 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
229910052707 ruthenium Inorganic materials 0.000 claims 1
239000000243 solution Substances 0.000 claims 1
125000003003 spiro group Chemical group 0.000 claims 1
QQWYQAQQADNEIC-RVDMUPIBSA-N tert-butyl [(z)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(/C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-RVDMUPIBSA-N 0.000 claims 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
- C—CHEMISTRY; METALLURGY
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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MEP-2013-511A 2008-01-18 2009-01-15 Inhibiteurs de bêta-lactamase ME02089B (fr)

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US1153308P	2008-01-18	2008-01-18
PCT/US2009/031047 WO2009091856A2 (fr)	2008-01-18	2009-01-15	Inhibiteurs de bêta-lactamase
EP09701487.2A EP2231667B1 (fr)	2008-01-18	2009-01-15	Inhibiteurs de bêta-lactamase

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ECSP10010568A (es)	2010-11-30
KR101648728B1 (ko)	2016-08-17
US8487093B2 (en)	2013-07-16
NO2020024I1 (no)	2020-08-10
PL2666774T3 (pl)	2015-06-30
HRP20150269T1 (hr)	2015-04-24
CY2020025I1 (el)	2020-11-25
US20130274475A1 (en)	2013-10-17
HK1143809A1 (en)	2011-01-14
SI2231667T1 (sl)	2013-12-31
ECSP10010345A (es)	2010-08-31
CY2020023I1 (el)	2020-11-25
ZA201005333B (en)	2011-04-28
BRPI0906871A2 (pt)	2020-07-28
HUS2000024I1 (hu)	2021-03-29
CY2020025I2 (el)	2020-11-25
RU2445314C9 (ru)	2013-04-10
NZ586861A (en)	2011-12-22
PT2231667E (pt)	2013-12-13
CN102827067A (zh)	2012-12-19
FR20C1032I2 (fr)	2022-07-29
LUC00165I2 (fr)	2021-08-16
AU2009206119C1 (en)	2016-05-26
EP2666774A1 (fr)	2013-11-27
HN2010001395A (es)	2012-11-12
CN101918407B (zh)	2014-02-26
HK1186180A1 (en)	2014-03-07
JP5038509B2 (ja)	2012-10-03
WO2009091856A2 (fr)	2009-07-23
ES2533826T3 (es)	2015-04-15
CN101918407A (zh)	2010-12-15
EP2666774B1 (fr)	2015-01-07
CY1116243T1 (el)	2017-03-15
CA2712783A1 (fr)	2009-07-23
CY1114900T1 (el)	2016-12-14
LTPA2020517I1 (lt)	2020-07-27
FR20C1030I1 (fr)	2020-02-10
NO2020023I1 (no)	2020-08-10
HUS000513I2 (hu)	2021-03-29
WO2009091856A3 (fr)	2009-12-03
NI201000115A (es)	2011-07-08
UA101966C2 (en)	2013-05-27
DK2231667T3 (da)	2013-12-16
CY2020024I2 (el)	2020-11-25
RS53862B1 (sr)	2015-08-31
LTPA2020518I1 (lt)	2020-07-27
DK2666774T3 (en)	2015-03-23
JP5597164B2 (ja)	2014-10-01
IL206395A0 (en)	2010-12-30
FR20C1031I2 (fr)	2022-07-29
EP2231667B1 (fr)	2013-09-04
LTPA2020516I1 (lt)	2020-07-27
FR20C1031I1 (fr)	2020-02-10
HRP20131123T1 (hr)	2013-12-20
NL301051I2 (nl)	2020-09-03
CY2020023I2 (el)	2020-11-25
PT2666774E (pt)	2015-04-13
EP2231667A2 (fr)	2010-09-29
KR20160099117A (ko)	2016-08-19
CR11626A (es)	2010-09-13
NO2020022I1 (no)	2020-08-10
MA32025B1 (fr)	2011-01-03
MX2010007823A (es)	2010-08-10
IL206395A (en)	2015-04-30
SI2666774T1 (sl)	2015-04-30
PL2231667T3 (pl)	2014-01-31
AU2009206119B2 (en)	2012-06-07
RU2445314C1 (ru)	2012-03-20
FR20C1032I1 (fr)	2020-02-10
JP5422020B2 (ja)	2014-02-19
US20110294777A1 (en)	2011-12-01
NL301050I2 (nl)	2020-09-03
CO6331438A2 (es)	2011-10-20
HUS2000023I1 (hu)	2021-03-29
CN102827067B (zh)	2015-09-23
MY162532A (en)	2017-06-15
LTC2231667I2 (lt)	2021-07-26
DOP2010000218A (es)	2010-08-31
CY2020024I1 (el)	2020-11-25
KR20100130176A (ko)	2010-12-10
FR20C1030I2 (fr)	2021-08-27
KR101800610B1 (ko)	2017-11-23
RS53052B (sr)	2014-04-30
LTC2666774I2 (lt)	2022-01-25
JP2012214475A (ja)	2012-11-08
ES2433744T3 (es)	2013-12-12
HUS000504I2 (hu)	2021-03-29
BRPI0906871B1 (pt)	2021-09-28
JP2011510012A (ja)	2011-03-31
AU2009206119A1 (en)	2009-07-23
CA2712783C (fr)	2013-03-19
JP2011207900A (ja)	2011-10-20

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